|Live Racing at Keeneland, in Lexington, Kentucky|
I am not from Kentucky, but I lived there for 13.5 years, I own property there, I maintain a professional license there, which means this is a major holiday. Derby Day is always the first Saturday in May. It is hard to describe what an event it is for the state. It is the start of the run for the triple crown, requiring a single horse to win three very competitive and very different races in a single season, a feat no one has accomplished a couple of decades. For Kentucky the Derby is the biggest race, the most people, the best horses, the most money wagered. I have never been to the Derby (with an "e" not an "a",) I have watched it at Keeneland and at parties. I bet on it one year in Vegas.
Until I lived in Kentucky I had never been to a horse race. Growing up, horse racing was somehow taboo, yet my parents went to Vegas and bought lottery tickets. Somehow horse racing was different. And it really is. Horse racing is elegant, and at the same time has a blue-collar following. Owning competitive horses is a hobby for the very wealthy, it is fair to say that more money is spent owning horses, then is made by owning them. Occasionally a long-shot from humble beginnings blows the field away and makes the owner wealthy, but most of the small farmers just hope to produce a crop of foals that sells for more than it costs most years.
When you have a chance you should go watch live racing at one of the classic tracks. There are two classic racecourses in Kentucky. Churchill Downs in Louisville is home to the Derby. Unless you have thousands of dollars to spend, don't think about going to the Derby. For a hundred dollars or so you can get into the infield and watch the race on the jumbo-trons, why not stay home and avoid the crowd. Churchill Downs is a great place to go for racing anytime except for Derby weekend. Keeneland in Lexington is even more traditional. Keeneland is beautiful, it was modeled after Saratoga Springs in New York. Keeneland only runs live racing about 10 weeks out of the year, and really doesn't need to make a profit on racing. Keeneland's money and fame come from horse sales - several each year attracting big horses and big money. When I lived near there, I knew when the big sales were on, because the privately owned 747's would show up at Bluegrass Airport, Keeneland is directly across the street from the airport. Attending the sales is another thrill - and a free one unless you decide to buy something.
But the Derby is the big draw. People come from around the world. I was flying out of Lexington one morning the day after the Derby. Off to one side was a British Airways jet, loading the Queen's hat boxes into the cargo compartment, the Queen had been in town for the Derby, when I boarded my flight, William Shatner was in the front row, he now owns a farm in the area, he had been in town for the Derby.